"Capt. Neal®" wrote in message

This all begs the question of at what point does an overtaking situation
actually start? Where does the sailing rule end and the overtaking rule
take over. I say it never does unless the windward vessel fails to follow
the sailing rules and creates a close quarters situation.

Ah, I see what you're saying - the leeward boat could be overtaking, at
which point he becomes the give-way, rather than the stand-on vessel. I
don't know what it says in the colregs, but the RRS has stuff about overlaps
which could be used to define precisely when the overtaking maneuvre is
happening.